
Woolford Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Your Woolford Vacation
Say bye-bye to the stress of planning and hello to a Woolford vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Downtown Cambridge, which is good for bars and pubs, culture and cafes. In the mood for a bit of sightseeing? A trip to Woolford wouldn't be complete without checking out Harriet Tubman Underground Railroad National Historical Park, Spocott Windmill and other major attractions. Your ideal Woolford vacation is just clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.
Woolford Hotel Deals

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.8/10 Exceptional! (10 reviews)
Blue Heron
"Plenty of room, well stocked kitchen, great spaces. Kayaks and ping pong big hit. Outdoor spaces was good, although high tide and rain made it swampy. Screened in porch looking out to water a treat."
Reviewed on Jun. 19, 2025

Solomons Inn Resort & Marina
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Jul 13 to Jul 14
CA $196
per night
Jul 13 - Jul 14
7.8/10 Good! (822 reviews)
"Wonderful stay and the king suite was amazing! Pool was big. And breakfast was mostly grab n go but plentiful. We will definitely be back! Staff was very nice!"
Reviewed on Jul. 6, 2025

Hyatt Regency Chesapeake Bay
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is CA $312 per night from Jul 21 to Jul 22
CA $312
per night
Jul 21 - Jul 22
8.6/10 Excellent! (1,003 reviews)
"The Hyatt is a great stay. Balconies outside need painting. Staff and amenities otherwise are great."
Reviewed on Jun. 22, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.